Cyclopropane

cyclopropane

[¦sī·klō′prō‚pān]

(organic chemistry)

C₃H₆ A colorless gas, insoluble in water; used as an anesthetic.

McGraw-Hill Dictionary of Scientific & Technical Terms, 6E, Copyright © 2003 by The McGraw-Hill Companies, Inc.

The following article is from The Great Soviet Encyclopedia (1979). It might be outdated or ideologically biased.

Cyclopropane

 

(also trimethylene), an alicyclic hydrocarbon having the structural formula

Cyclopropane is a colorless gas with a boiling point of –32.8°C and a density of 0.720 g/cm³ at –79°C. Insoluble in water, it is soluble in alcohol and ether.

Cyclopropane is the first member of the homologous series of cycloparaffins. Its trimethylene ring, however, is characterized by reactions of the C═C double bond; for example, it forms 1,3-dibromopropane (BrCH₂CH₂CH₂Br) in its reaction with bromine. The cyclopropane ring is easily broken because it is strained. Nevertheless, in contrast to olefins, cyclopropane does not react with potassium permanganate and ozone at 20°C. Cyclopropane and hydrocarbons containing the cyclopropane ring may be obtained by reacting zinc dust with derivatives that have two halogens attached at the 1 and 3 positions. They may also be obtained by other methods, including the joining of carbenes to olefins.

Cyclopropane and its derivatives are of great theoretical interest; for example, it has been discovered that compounds containing the cyclopropenyl cation have aromatic properties. The cyclopropane ring is found in biologically important natural compounds (seePYRETHRINS). Cyclopropane itself is used as an anesthetic.

The Great Soviet Encyclopedia, 3rd Edition (1970-1979). © 2010 The Gale Group, Inc. All rights reserved.